Radical polymerizable monomers having a primary amine structure and polymerizates thereof are currently used in biomedical applications (such as drugs and gene carriers), polymeric surfactants, shampoo compositions, hydrophilic members and coating materials and other applications. However, such radical polymerizable monomers are very difficult to synthesize and have poor storage stability, which limit sufficient development in their use.
JP-A-61-68456 describes N-aminoalkyl (meth)acrylamides, for example, N-(2-aminoethyl)acrylamide and N-(3-aminopropyl)methacrylamide, and a method for preparing the same. However, these (meth)acrylamide compounds thus obtained tend to discolor, undergo thermal polymerization or become unstable during storage with the lapse of time.
JP-A-50-89407 describes a phosphate of an aminoalkylacrylate. However, the phosphate compound is converted to a hydroxyalkyl acrylamide with the lapse of time, implying inferior storage stability.
Journal of Polymer Science: Part A: Polymer Chemistry, Vol. 46, 4984-4996 (2008) discloses a methacrylamide hydrochloride, having a primary amine structure, such as, for example, N-(2-aminoethyl)methacrylamide hydrochloride. Similar to general hydrochlorides, however, the methacrylamide hydrochloride causes corrosion of metals due to the presence of the halide ion. Moreover, an aqueous solution of the methacrylamide hydrochloride is strongly acidic and undergo thermal polymerization during storage which is problematic.